Michael Anthony Claudio Wincott was born to an English father and Italian mother in Scarborough, a working-class suburb of Toronto. His career began fortuitously in 1976 at the CBC, where he was cast by Deidre Bowen, Clare Walker, and director Mike Newell as the troubled protagonist, Cole Buckley, opposite Kate Reid in writer Rochelle Kosar's Earthbound.
He continued his novitiate in the city's leading contemporary theaters, working with Ken Gass at Factory Theatre Lab, Bill Glassco at The Tarragon Theatre, and William Lane at Toronto Free Theatre. Supported by grants from The Ontario Arts Council and The Canada Council of The Arts, he moved to New York City to study on a full scholarship at The Juilliard School.
During his time at Juilliard, he performed in various roles, including Teddy in Mark Medoff's When You Comin' Back Red Ryder?, Flute in Shakespeare's A Midsummer Night's Dream, Soranzo in John Ford's T'is Pity She's A Whore, and Tilden in the school's much-lauded first production of a Sam Shepard play, Buried Child.
After graduating, he began a rewarding relationship with Joseph Papp's Public Theater both on and off Broadway, creating the role of Kent in Eric Bogosian's Talk Radio. He also originated the role of Stubbs in Shepard's States of Shock, appearing opposite John Malkovich.
Throughout his career, Wincott has had the privilege of working with some of cinema's most gifted reprobates, including Anthony Hopkins, Gary Oldman, Julian Schnabel, Gerard Depardieu, Jim Jarmusch, Ridley Scott, Richard Burton, Robert Mitchum, Dennis Hopper, Michael Cimino, Robert De Niro, Sean Penn, John Hurt, Javier Bardem, Benicio Del Toro, Terrence Malick, and Oliver Stone.
In addition to his impressive filmography, Wincott has expressed a wish to work with the great French actress, Isabelle Huppert. As Albert Camus so aptly put it, "The only way to deal with an unfree world is to become so absolutely free that your very existence is an act of rebellion."